Monkwearmouth, Sunderland born goalkeeper Jimmy Maidment began his football career with Robert Thompson’s works team in 1921 before moving south to join Football League Third Division (South) club Southend United in 1923, making his Football League debut against Newport County that September. After one season, during which he played infrequently, totalling 13 appearances, he moved on to Newport County where among others Maidment played alongside his uncle, Billy Charlton. Over the next six years, he made 231 appearances and, unusually for a goalkeeper, scored three goals, all from the penalty spot, including 2 in a week in October 1927. Having lost his place in December 1929 he left Newport in the 1930 close season joining Lincoln City as their regular goalkeeper, playing alongside his younger brother Tom as Lincoln finished as runners-up in the Third Division North. He missed only one League game making 43 appearances for The Imps in total. He then spent two seasons in the Second Division with Notts County making 45 appearances before finishing his career back in the third tier with Accrington Stanley, joining them in 1933 and making 43 appearances over a single season before returning to Nottingham to join non league Nottingham Co-operative Dairy in 1934.
His younger brother Tom Maidment was also a professional footballer for among others Lincoln City, Portsmouth and Cardiff City.